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Volume 67 
Part 6 
Page o1546  
June 2011  

Received 18 May 2011
Accepted 23 May 2011
Online 28 May 2011

[cv5096sup1]
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Key indicators
Single-crystal X-ray study
T = 113 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.092
Data-to-parameter ratio = 15.1
Details
Open access

2-Methyl-6-nitro-2H-indazole

Li Long,a Bing-Ni Liu,b* Mo Liub and Deng-Ke Liub

aSchool of Environmental and Chemical Engineering, Tianjin Polytechnic University, Tianjin 300160, People's Republic of China, and bTianjin Institute of Pharmaceutical Research, Tianjin, 300193, People's Republic of China
Correspondence e-mail: liudk@tjipr.com

In the title compound, C8H7N3O2, the molecular skeleton is almost planar with a maximum deviation of 0.0484 (9) Å for the methyl C atom. In the crystal, weak intermolecular C-H...N and C-H...O hydrogen bonds help to establish the packing.

Related literature

For the synthesis, see: Sorbera et al. (2006[Sorbera, L. A., Bolos, J. & Serradell, N. (2006). Drugs, 31, 585-589.]); Balardi et al. (1997[Balardi, P. G., Cacciari, B., Spalluto, G., Romagnoli, R., Braccioli, G., Zaid, A. N. & Pineda de las Infantas, M. J. (1997). Synthesis, 10, 1140-1142.]). For related structures, see: Qi et al. (2010[Qi, H.-F., Liu, B.-N., Liu, M. & Liu, D.-K. (2010). Acta Cryst. E66, o2955.]); Chen et al. (2009[Chen, Y., Fang, Z. & Wei, P. (2009). Acta Cryst. E65, o1775.]). For applications of indazole derivatives, see, for example: Li et al. (2008[Li, X. L., Wang, Y. B., Chen, H., Zhao, L. & Cao, K. Q. (2008). J. Hebei Univ. 28, 40-45.]).

[Scheme 1]

Experimental

Crystal data

  • C8H7N3O2

  • Mr = 177.17

  • Monoclinic, P 21 /c

  • a = 3.793 (3) Å

  • b = 12.200 (8) Å

  • c = 16.675 (11) Å

  • [beta] = 95.722 (9)°

  • V = 767.7 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 113 K

  • 0.40 × 0.20 × 0.10 mm
Data collection

  • Rigaku Saturn724 CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]) Tmin = 0.956, Tmax = 0.989

  • 7726 measured reflections

  • 1802 independent reflections

  • 1317 reflections with I > 2[sigma](I)

  • Rint = 0.039
Refinement

  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.092

  • S = 1.03

  • 1802 reflections

  • 119 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...N2i 0.95 2.52 3.446 (2) 164
C7-H7...O2ii 0.95 2.56 3.500 (2) 169
C8-H8A...O2iii 0.98 2.61 3.549 (2) 161
C8-H8B...O1ii 0.98 2.51 3.491 (2) 174
Symmetry codes: (i) -x, -y, -z+2; (ii) [x+1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (iii) -x+1, -y, -z+2.

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5096 ).

Acknowledgements

The authors thank Mr Hai-Bin Song of Nankai University for the X-ray crystallographic determination and for helpful suggestions.

References

Balardi, P. G., Cacciari, B., Spalluto, G., Romagnoli, R., Braccioli, G., Zaid, A. N. & Pineda de las Infantas, M. J. (1997). Synthesis, 10, 1140-1142.
Chen, Y., Fang, Z. & Wei, P. (2009). Acta Cryst. E65, o1775.  [CrossRef] [details]
Li, X. L., Wang, Y. B., Chen, H., Zhao, L. & Cao, K. Q. (2008). J. Hebei Univ. 28, 40-45.
Qi, H.-F., Liu, B.-N., Liu, M. & Liu, D.-K. (2010). Acta Cryst. E66, o2955.  [CSD] [CrossRef] [details]
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sorbera, L. A., Bolos, J. & Serradell, N. (2006). Drugs, 31, 585-589.  [ChemPort]

Acta Cryst (2011). E67, o1546  [ doi:10.1107/S1600536811019374 ]

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